There unfortunately isn't any clear cut answer to this. All women are different and have different experiences not only when they lost their virginity, but just having sex in general.
However, if after several times of having sex with this partner, you're still experiencing a lot of pain or discomfort, then you might have to consider that he's not doing correctly, or his penis is physically too big for you.
I think the key is being comfortable with your body being able to communicate with your partner about anything that doesn't feel good, and completely trusting your partner. Everything else is open to exploration.
And like they said above, you might not feel any pain at all.